''sec''-Butyl acetate, or ''s''-butyl acetate, is an
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
commonly used as a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
in
lacquer
Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity.
Asian lacquerware, which may be ca ...
s and
enamels, where it is used in the production of acyclic polymers, vinyl resins, and
nitrocellulose
Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...
. It is a clear
flammable liquid
A flammable liquid is a liquid which can be easily ignited in air at ambient temperatures, i.e. it has a flash point at or below nominal threshold temperatures defined by a number of national and international standards organisations.
The Occupat ...
with a sweet smell.
''sec''-Butyl acetate has three isomers that are also acetate esters:
''n''-butyl acetate,
isobutyl acetate
The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate (IUPAC name) or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacque ...
, and
''tert''-butyl acetate.
History
The first method of production of ''sec''-butyl acetate was the esterification of
''sec''-butanol and
acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a col ...
It was experimentally determined and published in 1946 by
Rolf Altschul Rolf is a male given name and a surname. It originates in the Germanic name ''Hrolf'', itself a contraction of ''Hrodwulf'' ( Rudolf), a conjunction of the stem words ''hrod'' ("renown") + ''wulf'' ("wolf"). The Old Norse cognate is ''Hrólfr''. A ...
.
Toxicology
The for rats is 13g/kg.
[Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.] Exposure in humans to significant quantities of ''sec''-butyl acetate can cause irritation to the eyes, mouth, throat, nose, and skin.
[International Programme on Chemical Safety. (2003). ''sec''-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.] Ingestion and inhalation of ''sec''-butyl acetate can cause central nervous system depression producing symptoms of dizziness and disorientation.
Nomenclature
''sec''-Butyl acetate is
chiral
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is distinguishable from ...
. It has one
stereocenter
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...
, carbon 2 in the ''sec''-butyl group. The names of the two
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
s are:
*
2''S'')-butan-2-ylacetate, (+)-''sec''-butyl acetate
*
2''R'')-butan-2-ylacetate, (-)-''sec''-butyl acetate
References
External links
ChemExpr.com
{{DEFAULTSORT:Butyl acetate, sec-
Ester solvents
Acetate esters
Sweet-smelling chemicals